3-Pentanamine → 5-Chloro-3-(2-chlorophenyl)-1-[4-(N-1-ethylpropylcarbamoyl)benzyl]-1,3-dihydro-3-dimethylaminoindol-2-one

HRID 965566Notes

Reaction equation

HRID 965566 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)[C:6](=[O:21])[C:5]2([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:22]([CH3:24])[CH3:23].C([CH:34]([NH2:37])[CH2:35][CH3:36])C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:49]2C=CC=C[C:48]=2N=N1.CCN(C(C)C)C(C)C>CCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](=[O:18])[N:37]([CH2:34][CH2:35][CH3:36])[CH2:48][CH3:49])=[CH:14][CH:13]=1)[C:6](=[O:21])[C:5]2([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:22]([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 120193-PentanamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 190764264-[5-Chloro-3-(2-chlorophenyl)-2,3-dihydro-3-dimethylamino-2-oxoindol-1-yl]methylbenzoic acid

Product 1

HCID 571035265-Chloro-3-(2-chlorophenyl)-1-[4-(N-1-ethylpropylcarbamoyl)benzyl]-1,3-dihydro-3-dimethylaminoindol-2-one

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

This compound is prepared according to the procedure described in step B of EXAMPLE 94 from 0.623 g of the compound obtained in step A of EXAMPLE 94 and 0.24 ml of 1-ethylpropylamine, in the presence of 0.605 g of BOP and in the presence of DIPEA in order to maintain a pH of 7. Chromatography on silica using a gradient of a hexane/AcOEt mixture (from 90/10; v/v to 70/30; v/v) as the eluent gives the expected product after crystallization from a DCM/hexane mixture. m=0.490 g. M.p.=208° C.

Workup

  1. customThis compound is prepared
  2. temperatureto maintain a pH of 7

Sources & evidence

ORD record
ord-daa80cc35f684cb6b9821b66282bd70f
Source dataset
uspto-grants-1998_06
Patent number
US05773612

Reaction notes

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